15 Best Things to Do in Windham (CT)

Windham in North-eastern Connecticut contains the city of Willimantic, which developed around a textile industry in the late 19th century.

There’s a fantastic little museum dedicated to the cotton mill was once so central to the city’s fortunes.

The hundreds of dainty 19th-century properties on Prospect Hill indicate the sort of wealth that the textile trade generated for Willimantic.

The city now has a real sense of togetherness and community, shown by the Third Thursday Street Fest in summer when artists and crafters from Willimantic and the wider area display their wares, paired with live music and great food.

2. Prospect Hill Historic District

Anyone with an eye for Victorian architecture will be besotted with this genteel corner of Willimantic that grew up between 1865 and 1930. The quantity of ornate 19th-century architecture is almost overwhelming; Prospect Hill has one of the largest single concentrations of buildings from this era in the state.

There are 993 contributing buildings, 600 of which are houses, more than half of which were completed before the turn of the century.

Prospect Hill is best discovered on foot, as you pick out your favorites in the Italianate, Second Empire, Queen Anne and Stick and Shingle styles.

3. Connecticut Eastern Railroad Museum

This lovable museum is found on the site of the old Columbia Junction Freight Yard, and preserves an exciting collection of original and replica railroad structures and vintage rolling stock.

The main building here is the Columbia Junction Roundhouse, reborn in the 1990s using the late-19th-century foundations of the original, and completed in 2001. Also here is Chaplin Station, constructed in 1872 and relocated to the museum site in 1995, and joined by the restored Groton Freight House a little later.

There are some impressive locomotives to size up too, like an EMD SW8, used from shunting/switching and a New Haven EMD FL9, both from the 1950s.

A great thing about the museum is that restoration works constantly taking place, so there’s always a lot of life when you visit.

The highlight of the calendar at the museum is Railroad Day at the end of August, bringing train rides, live music and all kinds of family fun.

4. Philip Lauter Park

A treasured public space, Philip Lauter Park has an idyllic location next to the Natchaug River, and is crammed with amenities for all the family.

In summer the headline is the Splash Park and Waterfront, open from mid-June to the end of August for swimming in the gentle river and running wild among the fountains and spouts.

There are also conventional playgrounds for children, as well as a well-equipped skate park, basketball court, pavilions, open lawns and picnic tables.

Philip Lauter Park is also a popular fishing spot and has a community garden in great health.

5. Mansfield Hollow Lake

Source: Jeff Holcombe / shutterstock

Mansfield Hollow Lake

This reservoir on Windham’s northern boundary provides drinking water for Willimantic and controls flooding in the Thames River watershed.

Mansfield Hollow Lake was created at the turn of the 1950s and the dam site has been listed on the National Register of Historic Places since 2003. Mansfield Hollow State Park is on the western shore, and has trails for hiking, mountain biking and cross-country skiing.

You can pick up the Nipmuck Trail here, which courses through Mansfield’s wilderness for 35 miles.

The dam itself is also a much loved spot for hiking, with picnic areas both by the lake and downstream from the dam.

6. Allanach-Wolf Woodlands

Based in Mansfield, Joshua’s Tract Conservation and Historic Trust was incorporated in 1966 to help conserve areas of natural or historic interest.

One such property can be found in Windham at the Allanach-Wolf Woodlands, more than 120 acres of mostly forested land, donated to the trust by Ada Wolf in 2007. The woods are laced with streams, which flow into the 22-acre shallow pond called Lake Marie.

Marked trails weave off into the woods and there’s a lovely little butterfly garden that bursts into color in spring and summer.

People from the 860 Rocks facebook group hide painted stones for others to discover here.

9. Kerri Art Studio and Gallery

This late-19th-century store on 861 Main Street is the base for artist Kerri Quirk, who is something of an outsider, having earned a great deal of praise deviating from the conventions of the art world.

Both deaf and with autism, Kerri’s work is fresh, bright, fun and confrontational.

She paints here five days a week, while the gallery hangs exhibitions of her work, as well as revolving shows by local and not so local artists.

Along with originals, Kerri’s art is printed on mugs, clothing and more.

There’s regular live music, group paint nights and the gallery participates in the Third Thursday Street Fest which we’ll talk about below.

10. Prudence Crandall Museum

A simple drive east on Connecticut Route 14 will bring you to the home of the abolitionist Prudence Crandall (1803-1890), Connecticut’s official state heroine.

Between 1832 and 1834 she ran the “Prudence Crandall School for Negro Girls” here, which was shut down because of mob violence.

Crandall endured three court trials for her determination to provide private education for young African American women.

At the property there are four period rooms where you can walk in the footsteps of Crandall and her students, while the galleries go into more depth on Crandall’s story and the landscape in America at the time, with three changing exhibitions.

There’s also a research library and a gift shop, and it’s worth giving yourself some time to wander the house’s landscaped grounds.

14. Third Thursday Street Fest

Between May and September Main Street is flooded with people every third Thursday evening of the month for an event that has been going strong since 2002. Ambling through the Third Thursday Street Fest you’ll be greeted by live music, street theatre and more than 100 vendors from Willimantic and the wider region.

You’ll get to see the full breadth of arts and crafts produced in Connecticut, and of course there’s craft beer, local wine and delicious international cuisine to make clear just how diverse Willimantic is.

Main Street is divided into color-coded sections during the event and in the Uptown Area there’s a children’s space with lots of things to keep wee ones engaged.

15. Boom Box Parade

Willimantic’s annual Boom Box Parade has taken place every 4th of July since 1986. The tradition was born when no marching band could be found for Windham’s Memorial Day parade, and five weeks later for Independence Day the local radio station WILI-AM played the marching band music on the air for people to tune in and play from boom boxes as they marched.

Anybody can take part, and the only prerequisite is to be wearing some red, white and blue and carry a radio tuned to WILI (1400-AM). No pre-registration is needed, and the crowd gathers at Jillson Square by Main Street at 09:00 on July 4.